Tag: 100-200

Aryne approach towards 2,3-difluoro-10-(1H-1,2,3-triazol-1-yl)pyrido[1,2-a]indoles was written by Kopchuk, Dmitry S.;Nikonov, Igor L.;Zyryanov, Grigory V.;Nosova, Emiliya V.;Kovalev, Igor S.;Slepukhin, Pavel A.;Rusinov, Vladimir L.;Chupakhin, Oleg N.. And the article was included in Mendeleev Communications in 2015.Application of 774-47-0 This article mentions the following:

Reaction between 3-(2-pyridyl)-1,2,4-triazines and in situ generated 4,5-difluorobenzyne in toluene affords 2,3-difluoro-10-(1H-1,2,3-triazol-1-yl)pyrido[1,2-a]indoles. The structure of one representative compound was confirmed by X-ray diffraction anal. In the experiment, the researchers used many compounds, for example, 5,6-Difluoroindoline-2,3-dione (cas: 774-47-0Application of 774-47-0).

5,6-Difluoroindoline-2,3-dione (cas: 774-47-0) belongs to indole derivatives. Indole is an important structural motif of various drugs, therapeutic leads besides its prevalence in numerous natural products, agrochemicals, perfumery, and dyes. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Application of 774-47-0

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Carbene-Catalyzed Enantioselective Aromatic N-Nucleophilic Addition of Heteroarenes to Ketones was written by Liu, Yonggui;Luo, Guoyong;Yang, Xing;Jiang, Shichun;Xue, Wei;Chi, Yonggui Robin;Jin, Zhichao. And the article was included in Angewandte Chemie, International Edition in 2020.Safety of 5,6-Difluoroindoline-2,3-dione This article mentions the following:

The aromatic nitrogen atoms of heteroarylaldehydes were activated by carbene catalysts to react with ketone electrophiles. Multi-functionalized cyclic N,O-acetal products I [R¹ = H, 8′-Br, 7′-Cl, etc.; R² = H, 4-Br, 5-Cl, etc.; R³ = Me, Bn, Trt], II [R¹ = H, 8-Br, 7-F, etc.; R² = H, 3-Me, 4-Cl, etc.; R³ = Me, Et, Ph, Bn, CHPh₂] and III [R¹ = H, 6;t-Bu, 7’Cl, etc.; R² = H, 4-Cl, 5-Me, etc.] were afforded in good to excellent yields and optical purities. Reaction involved the formation of an unprecedented aza-fulvene-type acylazolium intermediate. A broad range of N-heteroaromatic aldehydes and electron-deficient ketone substrates works effectively in this transformation. Several of the chiral N,O-acetal products afforded through this protocol exhibited excellent antibacterial activities against Ralstonia solanacearum (Rs) and are valuable in the development of novel agrichems. for plant protection. In the experiment, the researchers used many compounds, for example, 5,6-Difluoroindoline-2,3-dione (cas: 774-47-0Safety of 5,6-Difluoroindoline-2,3-dione).

5,6-Difluoroindoline-2,3-dione (cas: 774-47-0) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Safety of 5,6-Difluoroindoline-2,3-dione

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Nickel supported on magnetic biochar as a highly efficient and recyclable heterogeneous catalyst for the one-pot synthesis of spirooxindole-dihydropyridines was written by Dong, Li-Na;Wang, Ya-Meng;Zhang, Wan-Lu;Mo, Li-Ping;Zhang, Zhan-Hui. And the article was included in Applied Organometallic Chemistry in 2022.Computed Properties of C8H3F2NO2 This article mentions the following:

Magnetic materials show promising applications in heterogeneous catalysis because of their ease of separation and good reusability. The present work reports the design, synthesis, and characterization of a novel magnetic biochar supported nickel catalyst. Fourier IR spectroscopy (FT-IR), powder X-ray diffraction technol. (XRD), scanning electron microscope (SEM), transmission electron microscope (TEM), and vibrating sample magnetometer (VSM) techniques were used for analyzing the prepared catalyst. The prepared catalyst exhibited excellent catalytic activity for synthesis of spirooxindole-dihydropyridine derivatives by a one-pot three-component reaction of isatin, barbituric acid, and 6-amino uracil or 1H-pyrazol-5-amine. This new methodol. demonstrated some important features, including high yields, lower loading of the catalyst, easy work-up, and recyclability of the catalyst for a min. of six times without an obvious decay of catalytic performance. In the experiment, the researchers used many compounds, for example, 5,6-Difluoroindoline-2,3-dione (cas: 774-47-0Computed Properties of C8H3F2NO2).

5,6-Difluoroindoline-2,3-dione (cas: 774-47-0) belongs to indole derivatives. In addition to tryptophan, indigo, and indoleacetic acid, numerous compounds obtainable from plant or animal sources contain the indole molecular structure. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Computed Properties of C8H3F2NO2

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Synthesis of dihydrocarbazoles via (4+2) annulation of donor-acceptor cyclopropanes to indoles was written by Liu, Changhui;Zhou, Li;Huang, Wenbo;Wang, Man;Gu, Yanlong. And the article was included in Tetrahedron in 2016.Reference of 4769-96-4 This article mentions the following:

Dihydrocarbazoles were synthesized through a novel [4+2] annulation of donor-acceptor cyclopropanes (DACs) to indoles. This reaction was performed in ethanol by using para-toluenesulfonic acid as catalyst. Mechanism of this reaction might involve the following three steps: (i) an electrophilic ring-opening reaction of the DACs with indoles, in which C3 position of indole acts as a nucleophilic site, (ii) an intramol. dehydration induced ring-closing reaction occurs that offers a spiro intermediate, and (iii) a following 1,2-migration which leading to a dihydrocarbazole scaffold. Otherwise, dihydroisoindole can also be constructed by replacing the indole component with pyrrole as nucleophile. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Reference of 4769-96-4).

6-Nitro-1H-indole (cas: 4769-96-4) belongs to indole derivatives. In addition to tryptophan, indigo, and indoleacetic acid, numerous compounds obtainable from plant or animal sources contain the indole molecular structure. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Reference of 4769-96-4

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Synthesis and evaluation of in vivo antioxidant, in vitro antibacterial, MRSA and antifungal activity of novel substituted isatin N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thiosemicarbazones was written by Nguyen, Dinh Thanh;Nguyen, Thi Kim Giang;Quyen, Tran Ha;Huong, Doan Thi;Toan, Vu Ngoc. And the article was included in European Journal of Medicinal Chemistry in 2016.Category: indole-building-block This article mentions the following:

Some new isatin N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thiosemicarbazones, e.g. I, with different substituents at 1-, 5- and 7-positions of isatin ring have been synthesized by reaction of N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thiosemicarbazide 2 with corresponding isatins. Title compounds were evaluated in vivo for antioxidant activity and in vitro for anti-microorganism activities. The MIC values were found for Gram pos. bacteria (MIC = 1.56-6.25 μM), for Gram neg. bacteria (MIC = 12.5 μM), and for fungi Aspergillus niger (MIC = 3.12-12.5 μM), Fusarium oxysporum (MIC = 6.25-12.5 μM) and Saccharomyces cerevisiae (MIC = 6.25-12.5 μM). Regarding the antioxidant activity, the SOD, GHS-Px and catalase activities of were MIC = 10.57-10.85, 0.27-0.93 and 345.45-399.75 unit/mg protein, resp. CompoundI showed the selective cytotoxic effects against some cancer (LU-1, HepG2, MCF7, P338, SW480, KB) cell lines and normal fibroblast cell line NIH/3T3. In the experiment, the researchers used many compounds, for example, 5-Isopropylindoline-2,3-dione (cas: 150560-58-0Category: indole-building-block).

5-Isopropylindoline-2,3-dione (cas: 150560-58-0) belongs to indole derivatives. Indole, also called Benzopyrrole, a heterocyclic organic compound occurring in some flower oils, such as jasmine and orange blossom, in coal tar, and in fecal matter. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Category: indole-building-block

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Bronsted-Acid-Promoted Rh-Catalyzed Asymmetric Hydrogenation of N-Unprotected Indoles: A Cocatalysis of Transition Metal and Anion Binding was written by Wen, Jialin;Fan, Xiangru;Tan, Renchang;Chien, Hui-Chun;Zhou, Qinghai;Chung, Lung Wa;Zhang, Xumu. And the article was included in Organic Letters in 2018.Safety of 2-Methyl-6-nitro-1H-indole This article mentions the following:

In the presence of [Rh(cod)Cl]₂, the thiourea-substituted ferrocenyldiphosphine ZhaoPhos, and HCl in AcOH, 2-alkyl- and 2,3-dialkyl-substituted N-unprotected indoles underwent diastereoselective and enantioselective hydrogenation to yield nonracemic indolines such as (S)-2-methylindoline and (S,S)-2,3-dimethylindoline in 48-99% yields and 82-98% ee; hydrogenation of 6-nitro-2-methylindole and 2-phenylindole gave products in low or no yield. DFT calculations of the relative free energies of transition states and intermediates in the hydrogenation of 2-methylindole support an outer-sphere mechanism for the hydrogenation; complexation of ZhaoPhos with chloride and DFT calculations indicate that anion binding is an important secondary interaction in catalysis. In the experiment, the researchers used many compounds, for example, 2-Methyl-6-nitro-1H-indole (cas: 3484-23-9Safety of 2-Methyl-6-nitro-1H-indole).

2-Methyl-6-nitro-1H-indole (cas: 3484-23-9) belongs to indole derivatives. In addition to tryptophan, indigo, and indoleacetic acid, numerous compounds obtainable from plant or animal sources contain the indole molecular structure. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Safety of 2-Methyl-6-nitro-1H-indole

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Enantioselective Synthesis of Cyclohepta[b]indoles: Gram-Scale Synthesis of (S)-SIRT1-Inhibitor IV was written by Gritsch, Philipp J.;Stempel, Erik;Gaich, Tanja. And the article was included in Organic Letters in 2013.Quality Control of 5-Chloroindole-3-carboxaldehyde This article mentions the following:

An enantioselective gram-scale synthesis of one of the most potent SIRT1-inhibitors, I, has been accomplished by an unprecedented domino reaction Wittig reaction/divinylcyclopropane rearrangement sequence establishing the cyclohepta[b]indole core. This method was developed for application in natural product synthesis of a variety of indole alkaloids. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Quality Control of 5-Chloroindole-3-carboxaldehyde).

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) belongs to indole derivatives. Indole, also called Benzopyrrole, a heterocyclic organic compound occurring in some flower oils, such as jasmine and orange blossom, in coal tar, and in fecal matter. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Quality Control of 5-Chloroindole-3-carboxaldehyde

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Identification of the First Highly Subtype-Selective Inhibitor of Human GABA Transporter GAT3 was written by Damgaard, Maria;Al-Khawaja, Anas;Vogensen, Stine B.;Jurik, Andreas;Sijm, Maarten;Lie, Maria E. K.;Baek, Mathias I.;Rosenthal, Emil;Jensen, Anders A.;Ecker, Gerhard F.;Froelund, Bente;Wellendorph, Petrine;Clausen, Rasmus P.. And the article was included in ACS Chemical Neuroscience in 2015.Safety of 5-Isopropylindoline-2,3-dione This article mentions the following:

Screening a library of small-mol. compounds using a cell line expressing human GABA transporter 3 (hGAT3) in a [³H]GABA uptake assay identified isatin derivatives as a new class of hGAT3 inhibitors. A subsequent structure-activity relationship (SAR) study led to the identification of hGAT3-selective inhibitors (i.e., compounds 20 and 34) that were superior to the reference hGAT3 inhibitor, (S)-SNAP-5114, in terms of potency (low micromolar IC₅₀ values) and selectivity (>30-fold selective for hGAT3 over hGAT1/hGAT2/hBGT1). Further pharmacol. characterization of compound 20 (5-(thiophen-2-yl)indoline-2,3-dione) revealed a noncompetitive mode of inhibition at hGAT3. This suggests that this compound class, which has no structural resemblance to GABA, has a binding site different from the substrate, GABA. This was supported by a mol. modeling study that suggested a unique binding site that matched the observed selectivity, inhibition kinetics, and SAR of the compound series. These compounds are the most potent GAT3 inhibitors reported to date that provide selectivity for GAT3 over other GABA transporter subtypes. In the experiment, the researchers used many compounds, for example, 5-Isopropylindoline-2,3-dione (cas: 150560-58-0Safety of 5-Isopropylindoline-2,3-dione).

5-Isopropylindoline-2,3-dione (cas: 150560-58-0) belongs to indole derivatives. Indole, also called Benzopyrrole, a heterocyclic organic compound occurring in some flower oils, such as jasmine and orange blossom, in coal tar, and in fecal matter. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Safety of 5-Isopropylindoline-2,3-dione

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Regioselective C3-Fluoroalcoholation of Indoles with Heptafluoroisopropyl Iodide via Palladium-Catalyzed C(sp²)-C(sp³) Cross-Coupling in the Presence of O₂ was written by Qin, Hong;Zhang, Zhen;Qiao, Kai;Chen, Xinran;He, Wei;Liu, Chengkou;Yang, Xiaobing;Yang, Zhao;Fang, Zheng;Guo, Kai. And the article was included in Journal of Organic Chemistry in 2022.Electric Literature of C8H6N2O2 This article mentions the following:

An efficient method for C3-fluoroalcoholation of indole derivatives was developed by merging C-F cleavage and C-C bond coupling, using free (NH)-indoles and heptafluoroisopropyl iodides as precursors. Preliminary mechanistic studies indicate that the bimetallic co-mediated C-F bond cleavage and the trifluoroacetate moiety play an essential role. Notably, this strategy constructs derivatizations through the modifiable carbon-oxygen bond. A broad range of structurally valuable organofluorine products was obtained, which shows excellent functional group tolerance. Furthermore, easily accessible materials were utilized and circumvented two troublesome steps of installing and removing an external auxiliary. This was the first report to introduce 3-fluoroalcoholated indoles via fluorohalides. This reaction offers a straightforward and efficient platform to access worthwhile fluorinated free (NH)-heteroarenes derivatives In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Electric Literature of C8H6N2O2).

6-Nitro-1H-indole (cas: 4769-96-4) belongs to indole derivatives. In addition to tryptophan, indigo, and indoleacetic acid, numerous compounds obtainable from plant or animal sources contain the indole molecular structure. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Electric Literature of C8H6N2O2

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Design and synthesis of matrine derivatives as novel anti-pulmonary fibrotic agents via repression of the TGFβ/Smad pathway was written by Li, Lingyu;Ma, Liyan;Wang, Dongchun;Jia, Hongmei;Yu, Meng;Gu, Yucheng;Shang, Hai;Zou, Zhongmei. And the article was included in Molecules in 2019.Reference of 4769-96-4 This article mentions the following:

A total of 18 matrine derivatives were designed, synthesized, and evaluated for their inhibitory effect against TGF-β1-induced total collagen accumulation in human fetal lung fibroblast MRC-5 cell lines. Among them, compound 3f displayed the most potent anti-fibrotic activity (IC50 = 3.3 ± 0.3 μM) which was 266-fold more potent than matrine. 3f significantly inhibited the fibroblast-to-myofibroblast transition and extracellular matrix production of MRC-5 cells. The TGF-β/small mothers against decapentaplegic homologs (Smad) signaling was also inhibited by 3f, as evidenced by inhibition of cytoplasm-to-nuclear translocation of Smad2/3 and suppression of TGF-β1-induced upregulation of TGF-β receptor type I (TGFβRI). Addnl., 3f exhibited potent inhibitory effects against TGF-β1-induced fibroblasts migration. These data suggested that 3f might be a potential agent for the treatment of idiopathic pulmonary fibrosis via repression of the TGFβ/Smad signaling pathway. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Reference of 4769-96-4).

6-Nitro-1H-indole (cas: 4769-96-4) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Reference of 4769-96-4

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles